ES2563323T5 - Procedimiento para la preparación de un sólido cristalino a partir de derivados de ácido glicin-N,N-diacético - Google Patents
Procedimiento para la preparación de un sólido cristalino a partir de derivados de ácido glicin-N,N-diacético Download PDFInfo
- Publication number
- ES2563323T5 ES2563323T5 ES10747834T ES10747834T ES2563323T5 ES 2563323 T5 ES2563323 T5 ES 2563323T5 ES 10747834 T ES10747834 T ES 10747834T ES 10747834 T ES10747834 T ES 10747834T ES 2563323 T5 ES2563323 T5 ES 2563323T5
- Authority
- ES
- Spain
- Prior art keywords
- diacetic acid
- crystalline
- acid derivatives
- preparation
- glycine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000000034 method Methods 0.000 title claims description 25
- 239000007787 solid Substances 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 6
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 title description 5
- 239000007921 spray Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000005469 granulation Methods 0.000 claims description 11
- 230000003179 granulation Effects 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 244000052616 bacterial pathogen Species 0.000 claims 1
- 239000000047 product Substances 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000012459 cleaning agent Substances 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- -1 transition metal salts Chemical class 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 239000008139 complexing agent Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000013042 solid detergent Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical class NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- CIEZZGWIJBXOTE-UHFFFAOYSA-N 2-[bis(carboxymethyl)amino]propanoic acid Chemical compound OC(=O)C(C)N(CC(O)=O)CC(O)=O CIEZZGWIJBXOTE-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05D—INORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C; FERTILISERS PRODUCING CARBON DIOXIDE
- C05D9/00—Other inorganic fertilisers
- C05D9/02—Other inorganic fertilisers containing trace elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/33—Amino carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/32—Organic compounds containing nitrogen
- C11D7/3245—Aminoacids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009038951A DE102009038951A1 (de) | 2009-08-26 | 2009-08-26 | Verfahren zur Herstellung eines kristallinen Feststoffes aus Glycin-N,N-diessigsäure-Derivaten mit hinreichend geringer Hygroskopizität |
| DE102009038951 | 2009-08-26 | ||
| PCT/EP2010/005219 WO2011023382A2 (de) | 2009-08-26 | 2010-08-25 | Verfahren zur herstellung eines kristallinen feststoffes aus glycin-n, n-diessigsäure-derivaten mit hinreichend geringer hygroskopizität |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2563323T3 ES2563323T3 (es) | 2016-03-14 |
| ES2563323T5 true ES2563323T5 (es) | 2024-10-16 |
Family
ID=43500504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10747834T Active ES2563323T5 (es) | 2009-08-26 | 2010-08-25 | Procedimiento para la preparación de un sólido cristalino a partir de derivados de ácido glicin-N,N-diacético |
Country Status (17)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009038951A1 (de) * | 2009-08-26 | 2011-03-03 | Inprotec Ag | Verfahren zur Herstellung eines kristallinen Feststoffes aus Glycin-N,N-diessigsäure-Derivaten mit hinreichend geringer Hygroskopizität |
| MX2012004170A (es) * | 2009-10-12 | 2012-05-08 | Basf Se | Metodo para producir un polvo que contiene una o mas sales de agente de complejacion. |
| DE102009060814A1 (de) | 2009-12-30 | 2011-07-07 | inprotec AG, 79423 | Verfahren zur Herstellung eines Feststoffs mit hinreichend geringer Hygroskopizität, der Glutaminsäure-N,N-diessigsäure (GLDA) oder ein Derivat davon enthält |
| BR112013006404A2 (pt) * | 2010-09-27 | 2016-07-05 | Basf Se | processo para produzir grânulos, formulação, e, usos dos grânulos e dos aglomerados prensados |
| US9227915B2 (en) * | 2011-05-03 | 2016-01-05 | Basf Se | Process for the preparation of a crystalline L-MGDA trialkali metal salt |
| GB2491619B (en) * | 2011-06-09 | 2014-10-01 | Pq Silicas Bv | Builder granules and process for their preparation |
| EP2931700B1 (en) | 2012-12-14 | 2019-08-28 | Nouryon Chemicals International B.V. | Crystalline particles of salts of glutamic acid n,n-diacetic acid |
| CN104854078A (zh) | 2012-12-14 | 2015-08-19 | 阿克佐诺贝尔化学国际公司 | 谷氨酸n,n-二乙酸的结晶颗粒 |
| US9745250B2 (en) | 2014-05-13 | 2017-08-29 | Akzo Nobel Chemicals International B.V. | Process to crystallize chelating agents |
| RU2728876C2 (ru) * | 2015-12-11 | 2020-07-31 | Басф Се | Способ получения гранул |
| CN109415662A (zh) * | 2016-06-20 | 2019-03-01 | 巴斯夫欧洲公司 | 粉末和颗粒以及制备该粉末和颗粒的方法 |
| BR112019017127A2 (pt) * | 2017-02-24 | 2020-04-14 | Basf Se | processo para produção de sal de metal alcalino de diacetato de metilglicina sólido, partículas sólidas de sal de metal alcalino de diacetato de metilglici-na, e, uso de partículas sólidas |
| EP3649103B1 (en) * | 2017-07-07 | 2022-03-30 | Nouryon Chemicals International B.V. | Process to prepare a solid composition of an amino acid diacetic acid |
| EP3802481A1 (en) | 2018-05-30 | 2021-04-14 | Basf Se | Process for making solid methylglycine diacetate (mgda) alkali metal salt, and solid particles |
| EP4459628A3 (en) | 2018-06-26 | 2024-12-18 | Juul Labs, Inc. | Devices for cessation of nicotine addiction |
| EP3898575B1 (en) | 2018-12-21 | 2023-02-15 | Nouryon Chemicals International B.V. | Crumbly phase composition of methylglycine n,n diacetic acid |
| KR102771094B1 (ko) | 2019-11-21 | 2025-02-24 | (주)아모레퍼시픽 | 고함량의 락테이트 금속염 및 실리콘계 오일의 혼합물을 포함하는 w/s형 화장료 조성물 |
| WO2021255525A1 (en) | 2020-06-19 | 2021-12-23 | Nouryon Chemicals International B.V. | Process to prepare a co granule of methylglycine n,n diacetic acid salts employing a crumbly phase composition of methylglycine n,n diacetic acid salts |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932316A (en) | 1974-11-13 | 1976-01-13 | The Procter & Gamble Company | Free flowing detergent compositions containing benzoate salts |
| JPH0678225B2 (ja) * | 1985-11-27 | 1994-10-05 | 株式会社林原生物化学研究所 | 脱水医薬品とその製造方法 |
| DE4319935A1 (de) * | 1993-06-16 | 1994-12-22 | Basf Ag | Verwendung von Glycin-N,N-diessigsäure-Derivaten als Komplexbildner für Erdalkali- und Schwermetallionen |
| JP4711471B2 (ja) | 1996-07-05 | 2011-06-29 | 三菱商事フードテック株式会社 | 結晶マルチトール及びそれを含有する含蜜結晶の製造方法 |
| DE19649681A1 (de) * | 1996-11-29 | 1998-06-04 | Basf Ag | Verfahren zur Herstellung eines kristallinen Feststoffes aus Glycin-N,N-diessigsäure-Derivaten mit hinreichend geringer Hygroskopizität |
| ATE310587T1 (de) * | 2001-04-13 | 2005-12-15 | Urea Casale Sa | Wirbelbettgranuliervorrichtung |
| DE102004032320A1 (de) * | 2004-07-02 | 2006-01-19 | Basf Ag | Mischpulver oder Mischgranulat auf Basis von MGDA |
| BRPI0813968A2 (pt) * | 2007-07-03 | 2015-07-14 | Basf Se | Processo para produzir um sólido de livre escoamento e estável em armazenagem, e, uso do sólido de livre escoamento e estável em armazenagem. |
| MX2010010779A (es) * | 2008-04-01 | 2010-12-21 | Unilever Nv | Preparacion de granulos que fluyen libres de acido metilglicina diacetico. |
| FR2935383B1 (fr) * | 2008-08-26 | 2010-10-01 | Pancosma Sa Pour L Ind Des Pro | Procede et dispositif pour la fabrication de complexes organometalliques en poudre. |
| CA2762507C (en) * | 2009-05-20 | 2018-08-21 | Basf Se | Process for the preparation of a powder comprising one or more derivatives of glycine-n,n-diacetic acid and/or one or more derivatives of glutamine-n,n-diacetic acid and methylglycine-n,n-diacetic acid trisodium salt powder |
| DE102009038951A1 (de) * | 2009-08-26 | 2011-03-03 | Inprotec Ag | Verfahren zur Herstellung eines kristallinen Feststoffes aus Glycin-N,N-diessigsäure-Derivaten mit hinreichend geringer Hygroskopizität |
| MX2012004170A (es) * | 2009-10-12 | 2012-05-08 | Basf Se | Metodo para producir un polvo que contiene una o mas sales de agente de complejacion. |
| GB2491619B (en) * | 2011-06-09 | 2014-10-01 | Pq Silicas Bv | Builder granules and process for their preparation |
-
2009
- 2009-08-26 DE DE102009038951A patent/DE102009038951A1/de not_active Withdrawn
-
2010
- 2010-08-25 BR BR112012004179A patent/BR112012004179B1/pt active IP Right Grant
- 2010-08-25 MX MX2012002244A patent/MX2012002244A/es active IP Right Grant
- 2010-08-25 EP EP10747834.9A patent/EP2470496B2/de active Active
- 2010-08-25 PL PL10747834.9T patent/PL2470496T5/pl unknown
- 2010-08-25 US US13/391,397 patent/US9376649B2/en active Active
- 2010-08-25 CA CA2771916A patent/CA2771916C/en not_active Expired - Fee Related
- 2010-08-25 AU AU2010288872A patent/AU2010288872A1/en not_active Abandoned
- 2010-08-25 JP JP2012525929A patent/JP5756107B2/ja active Active
- 2010-08-25 MY MYPI2012000735A patent/MY158464A/en unknown
- 2010-08-25 RU RU2012111127/04A patent/RU2551851C2/ru active
- 2010-08-25 CN CN201080037900.3A patent/CN102574775B/zh active Active
- 2010-08-25 SG SG2012009312A patent/SG178352A1/en unknown
- 2010-08-25 KR KR1020127007333A patent/KR101755736B1/ko not_active Expired - Fee Related
- 2010-08-25 ES ES10747834T patent/ES2563323T5/es active Active
- 2010-08-25 WO PCT/EP2010/005219 patent/WO2011023382A2/de active Application Filing
-
2012
- 2012-03-22 ZA ZA2012/02132A patent/ZA201202132B/en unknown
-
2016
- 2016-04-12 US US15/096,678 patent/US9751829B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2470496A2 (de) | 2012-07-04 |
| WO2011023382A3 (de) | 2011-05-12 |
| KR20120089470A (ko) | 2012-08-10 |
| SG178352A1 (en) | 2012-03-29 |
| PL2470496T3 (pl) | 2016-06-30 |
| RU2551851C2 (ru) | 2015-05-27 |
| EP2470496B1 (de) | 2016-01-06 |
| US9751829B2 (en) | 2017-09-05 |
| AU2010288872A1 (en) | 2012-03-08 |
| DE102009038951A1 (de) | 2011-03-03 |
| MY158464A (en) | 2016-10-14 |
| CN102574775B (zh) | 2014-09-24 |
| US20120149936A1 (en) | 2012-06-14 |
| WO2011023382A2 (de) | 2011-03-03 |
| EP2470496B2 (de) | 2024-03-27 |
| PL2470496T5 (pl) | 2024-07-15 |
| US9376649B2 (en) | 2016-06-28 |
| BR112012004179B1 (pt) | 2018-09-11 |
| RU2012111127A (ru) | 2013-10-10 |
| BR112012004179A2 (pt) | 2016-03-29 |
| CN102574775A (zh) | 2012-07-11 |
| CA2771916A1 (en) | 2011-03-03 |
| US20160221930A1 (en) | 2016-08-04 |
| ES2563323T3 (es) | 2016-03-14 |
| JP2013503119A (ja) | 2013-01-31 |
| KR101755736B1 (ko) | 2017-07-07 |
| CA2771916C (en) | 2017-07-25 |
| ZA201202132B (en) | 2013-05-29 |
| JP5756107B2 (ja) | 2015-07-29 |
| MX2012002244A (es) | 2012-03-29 |
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